[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:10][C:11]2([C:21]#[N:22])[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)[CH2:9][CH2:8]1.O.[OH-].[Na+]>CCOCC>[CH:7]1([CH2:10][C:11]2([CH2:21][NH2:22])[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)[CH2:9][CH2:8]1To a stirred suspension of lithium aluminium hydride (1M solution in ether; 94.9 ml; 94.9 mmol) at −78° C. was added a solution of 8-(cyclopropylmethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (14 g;63.264 mmol) in ether (40 ml) over 30 minutes and the mixture stirred cold for 1 hour, then allowed to warm to ambient temperature and stirred for 3 hours. The resultant mixture was cooled in an ice bath and to the mixture was added in turn water (2 ml), 15% NaOH solution (2 ml) and water (2 ml). The resultant white granular solid was collected on a filter and rinsed twice with diethyl ether. The filtrate was evaporated to give the crude product as a colourless oil (12 g). 1H NMR δ (ppm)(CDCl3): 3.93 (4H, s), 2.68 (2H, s), 1.63-1.57 (4H, m), 1.54-1.48 (4H, m), 1.25 (2H, d, J=6.6 Hz), 0.65-0.50 (1H, m), 0.46-0.40 (2H, m), 0.02 (2H, q, J=4.9 Hz). MS (m/e)=226.
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